Enantioresolution of Substituted 2-methoxy-6-oxo-1,4,5,6-tetrahydropvridine-3-carbonitriles on Macrocyclic Antibiotic and Cyclodextrin Stationary Phases

SS CHEN, YB LIU, DW ARMSTRONG, JI BORRELL, B MARTINEZTEIPEL, JL MATALLANA

Producción científica: Artículo en revista indizadaArtículorevisión exhaustiva

57 Citas (Scopus)

Resumen

Nine different 4-, or 5- substituted racemic pyridones were synthesized and resolved by reversed phase LC. Seven of the compounds showed complete or partial resolution on the vancomycin bonded phase column, while five compounds each were separated on both the teicoplanin and the beta-cyclodextrin chiral stationary phase (CSPs). No enantioselective separations were obtained on alpha- or gamma-cyclodextrin stationary phases. The antineoplastic agent methotrexate also was resolved. Structural factors that significantly altered enantioselectivity included: changing the pyridone substituent from the 4 to the 5 position or vice versa, changing the size of the substituent, changing the degree of unsaturation of the substituent and changing the nature and length of the substituent ''tether''. The enantioselectivity of the two related macrocyclic antibiotic CSPs are somewhat similar but not identical. This provides a highly useful optimization approach for these columns. Frequently, when partial enantioresolution is obtained on one antibiotic CSP, a complete resolution is obtained on the related column using identical elution conditions. It is apparent that these separations (and CSPs) are highly complementary to each other.
Idioma originalInglés
Páginas (desde-hasta)1495-1507
Número de páginas13
PublicaciónJournal of Liquid Chromatography
Volumen18
N.º8
DOI
EstadoPublicada - 1995

Huella

Profundice en los temas de investigación de 'Enantioresolution of Substituted 2-methoxy-6-oxo-1,4,5,6-tetrahydropvridine-3-carbonitriles on Macrocyclic Antibiotic and Cyclodextrin Stationary Phases'. En conjunto forman una huella única.

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